US1522089A - Azodyestuffs and process of making the same - Google Patents

Description

Patented Jan. 6, 1925.

UNITED STATES PATENT OFFICE.

N WAGNER, OF HOOHS T-ON-THE-HAIN, AND OTTO SOHS'I, OF HANAUON-THE- IAIN, GERMANY, ASSIGNORS T FARBWERKE VORM. MEISTEB LUCIUS & BRUN- mo, OF HOGHST-ON-THE-IAIN, GERMANY, A CORPORATION OF GERMANY.

AZODYESTUFFS AND PROCESS OF MAKING THE SAME.

4 I0 Drawing.

To all whom it may concern Be it known that we, HERMANN WAGNER and O'rro Sons'r, citizens of Germany, residin at. Hochst-on-the-Main, Germany, 5 and anau-on-the-Main, Germany, have ina. vented certain new and useful Im rovements in Azodyestufi's and Processes of aking the Same, of which the following is a specification.

We have found that dyestufi's or dyein s of excellent fastness are produced by coup ing the diazo-com ounds obtained from the alkyl-, arylan aralkylamides of the alkyloxy-3-ammo-1-benzoic acids with any ar 1- amides of the 2.3-hydroxynaphthoic acid.

B this process there are obtained dyestufl's 0 an excellent clear red tint with a blue hue possessing the important property of being utilizable for the production of fast aliza0 arine-pink-shades.

Examples.

in which X stands for any acid residue.

4. The material is padded with a solution of:

24,9 g. of 2.3-hydroxynaphthoic acid 4- 75 chloro-2-anisidide [SN H.OCH,.C1=1 2 5), 80 ccm. of caustic so a solution 22 B., g.

Application filed December 26, 1923. Serial No. 882,819.

soda solution 34* B., 3 ccm. of sodium Turkey red oil 50%, 50 com. of hot water are made up to 1 litre with cold water. The impregnated yarn is wound oil and dyed in the following diazo solution.

1,6 g. of 3amino-4-methoxy-l-benzoic acid anilide are (pasted with 1,7 ccm. of hydrochloric aci 22 B. and 25 ccm. of water, cooled b addition of 25 com. of ice and mixed whi e stirring with a solution of 0,5 ccm. of sodium nitrite in 10 ccm. of water. The whole is made up with cold water to 1 litre and before use mixed with 1,34 of sodium acetate.

A ter dyeing the material is well washed and soaped.

3. The material is padded with a solution of: 21,1 g. of 2.3-hydroxynaphthoic acid o-toluidide (CH,:NH,=1:2), 60 com. of

caustic soda solution 22 B., 20 g. of Para soap PN. made u to 1 litre.

Then there is ried and printed with the following colour:

24,2 of 3-amino-4-methox -1-benzoic acid ani ide are well pasted wit 140 com. of water and 24 ccm. of hydrochloric acid 22 Be, cooled with 150 g. of ice and there are added 8 g. of sodium nitrite dissolved in com. of water, the whole is stirred into 524 g. of tragacanth 1000, there are then added 60 g. of aluminium sulphate 1: 1 dissolved in water and, before use, 20 g. of sodium phosphate, ca.

The reactlon involved in the foregoing examples 1, 2 and 3 is as follows:

OOH:

of Para soap PN, made up to 1 litre, then printed with the printing colour mentioned in example 2.

The reaction involved in this example is similar to that of examples 1, 2 and 3, the formula of the 2.3-hydroxynaphthoic acid- 4-chloro-2-anisidide acid involved being:

(Ii ai OCH:

Diaeo-solution.

2,42 of 3-amino-4-methoxy-l-benzoic acid anilide are dissolved in 200 com. of warm water and 2,4 ccm. of hydrochloric acid 22 B. cooled with 600 com. of cold water and 100 g. of ice, then there are added 0,8 g. of sodium nitrite dissolved in 16 com. of water, and before use there are added 2 g. of sodium acetate, the whole is made up to 1 litre and, as above indicated, stirred into 3 12 g. of 2.3-hydroxynaphthoic acid 5- chloro 2 toluidide (NH.OH,.C1:1 2 4 10,5 com. of caustic soda solution 22 B., 136 g. of sulphate of barium made up to 1 litre.

The sodium salt of the 2.3-hydroxynaphthoic acid-5-chloro-2-toluidide of the foregoing example has the formula:

(so 4H9 6. The am is impregnated with the following so ution:

1,25 g. of h droxynaphthoic acid-4-chloro- 2-anisididc H.OCH,.C1=1:2: 5), 2,? com.

of caustic soda solution 34 B., 3 com. of'

sodium Turkey red oil 50 com. of hot water, with cold water made up to 1 litre.

The impregnated yarn is wound off and dyed with the following diazo-solution:

1,6 g. of 3-amino-4-methoxy-l-benzoic acid anilide are pasted with 1,7 ccm. of hydrochloric acid 22 B. and 25 com. of water, then cooled by addition of 25 com. of ice and mixed while stirring with a solution of 0,5 g. of sodium nitrite in 10 com. of water and with cold water made up to 1 litre, before use there are added 1,34 g. of sodium acetate.

After dyeing it is washed and soaped.

A clear pink with a blue hue is obtained.

If the 3-amino-4-methoxy-1-benzonic acid anilide; used in Ex. 6 is replaced by an equivalent quantity of 3-amino-4-ethoxy-1- benzoic acid anilide or of the 3-amino-4- methoxy-l-benzoic acid-2-toluidide, there are produced very similar pink shades, whereas y usin 3-amino-4-methoxy-1-benzoic acid ethylani ide there is obtained a pink with .a somewhat yellower hue. Pink shades all of a somewhat yellower hue, are roduced, if the 2.3-hydroxynaphthoic aci -4-chloro-2- anisidide, mentioned in example 6 is replaced by an equivalent quantity of 2.3-hydroxynaphthoic acid-5-chloro-2-toluidide, ((1H,:NH Cl:1:2:5) and if the latter is coupled with the aforesaid diazo-compounds.

. The 3-amino-4-ethoxy-1-benzoic-acid-ani lide, 3-amino--methoxy-l-benzoic acid-2- toluidide and 3-aminol-methoxy-l-benzoic aciril ethylanilide referred to have the formu 8e By alkyloxy-3-amino-1-benzoic acids we mean not only the parent compounds but also their homologues and substitution products.

Having now described our inventlon, what we claim is:

1. As new products the dyestuifs obtainable by coupling the diazo compounds of alkyl-aryl-and aralkyl amides of the alkyloxy-3-amino-1-benzoic acids with any 2.3-hydroxynaphthoic acid arylides which, on reduction eld an aromatic amino and an arylide of t e 1-amino-2-hydroXy-3-naphthoic-acid.

2. Process for preparing azo-dyestufis which consists in coupling the diazo compounds of alkylaryland aralkylamides of the alkyloxy-3-amino-1-benzoic acids with any 2.3-hydroxynaphthoic acid arylamides.

In testimony whereof, we aflix our signa- 0 tures.

HERMANN WAGNER. O'ITO SOHST.

2.3-hydroxynaphthoic acid arylides which, In testimony whereof, we afiix our signa- 10 on reduction 1eld an aromatic amine and an tures.

aryllde of t e 1-amino-2-hydro1iy-3-naphtholc-acid. HERMANN WAGNER. 5 Process for preparing azo-dyestufls OTTO SOHST.

which consists in coupling the diazo compounds of alkylaryland aralkylamides of Witdxessesz the alkyloxy-3-amino-1-benzoic acids with G. C. L. B. WYnns, any 2.3-hydroxynaphthoic acid arylamides. JANE Smnsrr.

Certificate of Correction.

It is hereby certified that in Letters Patent No. 1,522,089, granted January 6, 1925, upon the application of Hermann Wagner, of Hochst-on-the-Main, and Otto Sohst, of Hanau-on-the-Main, Germany, for an improvement in Azodyestufls and Processes of Making the Same, errors appear in the printed specification requiring correction as follows: Page 1, line 68, after ca. insert 1 kg; page 2, line 63, for the misspelled word ben zonic read benzoic; same page, line 93, following the formulae, insert the word respectively; and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent Oifice.

Signed and sealed this 10th day of March, A. D. 1925.

[HEAL] KARL FENNING,

Acting Commissioner of Patents.

Certificate of Correction.

It is hereby certified that in Letters Patent No. 1,522,089, granted January 6, 1925, upon the application of Hermann Wagner, of Hochst-on-the-Main, and Otto Sohst, of Hanau-on-the-Main, Germany, for an improvement in Azodyestuifs and Processes of Making the Same, errors appear in the printed specification requiring correction as follows: Page 1, line 68, after ca. insert 1 kg; page 2, line 63, for the misspelled word ben zonic read benzm'c; same page, line 93, following the formulae, insert the word respectively; and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent Oflice.

Signed and sealed this 10th day of March, A. D. 1925.

[smn] KARL FENNING,

Acting Gommiesiomr of Patents.